484696-92-6

Upstream product

• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 586-96-9 Nitrosobenzene 
• 227014-39-3 C₁₁H₂₄OSi₂ 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 108-94-1 cyclohexanone 

Downstream Products

• 33670-02-9 2-(phenylamino)cyclohex-2-en-1-one 
• 533-60-8 cyclohexanone-2-ol 

Relevant academic research and scientific papers

Sugar-assisted kinetic resolution of amino acids and amplification of enantiomeric excess of organic molecules

The origins of biological homochirality have intrigued researchers since Pasteur's discovery of the optical activity of biomolecules. Herein, we propose and demonstrate a novel alternative for the evolution of homochirality that is not based on autocataly

Nonlinear effects in asymmetric amino acid catalysis by multiple interconnected stereoselective catalytic networks

A fine line: The generation of significant positive nonlinear effects in asymmetric amino acid catalysis under homogeneous conditions, which can be explained by the model for cooperative catalytic stereoselective pathways, is reported. The addition of an achiral aldehyde generated the multiple interconnected stereoselective catalytic network.

Enantioselective O-nitroso aldol reaction of silyl enol ethers

(Chemical Equation Presented) New nucleophiles for the O-nitroso aldol reaction in the form of readily prepared disilanyl enol ethers make this transformation more practicaland more versatile. A silver catalyst with a chiral biaryl phosphite ligand promotes the title reaction with high enantio- and regioselectivity (see scheme). R1,R2 = H, Ar; TMS = trimethylsilyl.

PROCESS OF MAKING α-AMINOOXYKETONE/α-AMINOOXYALDEHYDE AND α-HYDROXYKETONE/α-HYDROXYALDEHYDE COMPOUNDS AND A PROCESS OF MAKING REACTION PRODUCTS FROM CYCLYC α,?-UNSATURATED KETONE SUBSTRATES AND NITROSO SUBSTRATES

The present invention is directed to a process of making α-aminooxyketone and α--hydroxyketone compounds. The synthetic pathway generally involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of formula (IV), wherein X1-X3 represent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the α-aminooxyketone compound formed to the α-hydroxyketone compound. The present invention results in α-aminooxyketone and α-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol / Michael reaction. The substrates of this reaction are generally cyclic α,?-unsaturated ketone substrate and a nitroso substrate. This methodology generally involves reacting the cyclic α,?-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

Bronsted acid catalysis of achiral enamine for regio- and enantioselective nitroso aldol synthesis

Two types of chiral Bronsted acid catalysts have been shown to catalyze regio- and enantioselective nitroso aldol synthesis between nitrosobenzene and achiral enamine. The combination of Bronsted acidity and amine moiety of enamine realizes complete regioselectivity with high enantioselectivity. After a survey of Bronsted acid catalysts, 1-naphthyl glycolic acid is found to be optimal in the O-nitroso aldol pathway, while 1-naphthyl TADDOL is the best catalyst for the N-nitroso aldol pathway. This is based on our finding on the control of regioselectivity by changing the amine moiety of enamine and the choice of Bronsted acidity. Copyright

Lewis acid promoted, O-selective, nucleophilic addition of silyl enol ethers to N=O bonds

Not N-adduct but O-adduct is formed in the Lewis acid catalyzed nucleophilic addition of silyl enol ethers 2 to the N=O bond of nitrosobenzene (1). Various Lewis acids (e.g. alkylsilyl triflates) efficiently catalyze the formation of the aminooxy ketone (